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linkedin-dm-outreach

This skill should be used when the user asks to "write a LinkedIn message", "draft a connection request", "help me reach out to someone on LinkedIn", "write an InMail", "message this person", or when the prospect-researcher skill identifies a high-value contact worth reaching out to. Also triggered by "how should I approach [person/company]" in a LinkedIn context.

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Works withLinkedIn

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SKILL.md (original)

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LinkedIn DM Outreach

Purpose

Write personalized LinkedIn messages — connection requests, InMails, and follow-up messages — that get responses instead of being ignored. Every message must demonstrate genuine relevance: why THIS person, why NOW, why the user is worth responding to.

Voice Loading

Load the user's voice via voice-master's overlay resolution before drafting:

  1. Read ../voice-master/SKILL.md and follow its User Calibration Overlay section to load exemplars and voice-dimensions from the out-of-repo overlay (or template fallback with warning if no overlay).
  2. This skill's medium is professional. Select professional-medium exemplars from whatever voice-master loads.
  3. Read ../voice-master/references/anti-slop.md — apply the Universal and Professional / LinkedIn sections.

If no overlay is present, voice-master falls back to generic voice guidance and warns — note this in your output.

DMs are the most personal LinkedIn format — sounding templated here is fatal. One bad outreach message can permanently close a door.

Message Types

Connection Request (300 characters max)

The hardest format. 300 characters to establish relevance and earn a click.

Rules:

  • Name a specific reason for connecting (shared interest, their content, mutual connection, specific role/company)
  • No generic "I'd love to add you to my network"
  • No pitching in the connection request — ever
  • If there's no genuine reason to connect, don't send the request

Structure: "[Specific reference to them or their work]. [Why connecting makes sense for both sides — in one sentence]."

First Message (after connecting)

Sent after a connection request is accepted, or to an existing connection.

Rules:

  • Thank them for connecting (brief, not gushing)
  • Reference something specific about them or their work
  • State your reason for reaching out clearly
  • Ask one specific question or make one specific offer
  • Keep under 150 words — respect their time
  • No "I hope this message finds you well"
  • No walls of text about yourself

Structure:

  • Line 1: Brief genuine acknowledgment
  • Line 2-3: Why you're reaching out (specific, relevant)
  • Line 4: One clear ask or offer

Follow-Up Message

If the first message got no response after 5-7 days.

Rules:

  • Maximum ONE follow-up. Two unanswered messages = they're not interested.
  • Add new value — don't just "bump" or "circle back"
  • Shorter than the first message
  • No guilt ("I know you're busy but...")
  • Accept that silence is an answer

Warm Introduction Request

Asking a mutual connection to introduce you to someone.

Rules:

  • Make it easy for the introducer — provide a brief, forwardable blurb
  • Explain why the introduction makes sense for all three parties
  • Never pressure — "only if you think it makes sense"

Research Integration

Before drafting any outreach, gather intelligence on the recipient:

  • Their recent posts and content (what they care about)
  • Their current role and company (what they're dealing with)
  • Mutual connections (potential introduction path)
  • Shared interests or background (common ground)
  • Their company's recent news (relevant context)

If the prospect-researcher skill has already run on this target, use its findings. If not, perform lightweight research before writing.

Outreach Scenarios

Job Search

Goal: Get a conversation about opportunities. Approach: Lead with what you can do for them, not what you want. Reference specific challenges their company/team faces. Ask about the team or the work, not about open positions directly.

Client Acquisition

Goal: Start a relationship that could lead to business. Approach: Never pitch in the first message. Offer genuine value first (insight, introduction, resource). Build rapport before discussing services. The goal is a conversation, not a sale.

Networking

Goal: Build a genuine professional relationship. Approach: Reference specific shared interests or complementary expertise. Suggest a concrete (low-commitment) next step — a specific article exchange, a brief call, a shared event.

Recruiting / Hiring

Goal: Attract a candidate. Approach: Lead with why you noticed THEM specifically (not "we have an exciting opportunity"). Be transparent about the role and company. Respect that they may not be looking.

Output Format

recipient: <name and context>
message_type: <connection_request | first_message | follow_up | intro_request>
scenario: <job_search | client_acquisition | networking | recruiting>
research_used: |
  <key findings about the recipient that informed the message>
message: |
  <the message text>
character_count: <for connection requests — must be under 300>
rationale: |
  <why this approach and angle>

References

  • ../voice-master/SKILL.md — Voice authority; follow its User Calibration Overlay section to load professional exemplars from the user overlay
  • ../voice-master/references/anti-slop.md — Universal + Professional/LinkedIn anti-slop rules
  • ../prospect-researcher/SKILL.md — Deep research on outreach targets

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